How to hire your first VP of Engineering

08 Mar, 2025

Huge thank you to Laura Hilton who helped me hire our VPE. I would have had to learn a lot more via trial and error without her help. And I hope this post brings some of her wisdom into the public to make other founders' lives easier!

Intro

Hiring your first executive is hard. Following a rigorous process can make it easier. In this post, I'll lay out a step-by-step guide (based on my experience) for hiring your first VP of Engineering: from deciding you need to hire to actually finding someone great.

If you've already hired excellent ICs (or even maybe a few managers), you can absolutely hire a VP.

This post is intended for founder/CTOs hiring a VPE, but I suspect the advice will be helpful for founders in other roles (e.g. CEO) and for those hiring VPs in other functions.

Prologue: Deciding the CTO's role¹

One of the most-common questions about hiring a VPE is figuring out what the founder/CTO will do after the VPE starts. You should figure this out before you decide to hire a VPE!

Companies have a few different common set ups for their CTO and which functions they oversee. If the CTO is the Head of Engineering, Product, and Design (EPD), hiring a VPE might make sense: the Head of EPD (CTO) continues to oversee all three functions and will likely hire (or already has hired) Heads of Product and Design over time.

Alternatively, if the CTO does not run Product (i.e. the CEO runs Product or there is a 3rd Product co-founder), the decision to hire can be more complicated. Often, the founder/CTO has been the de facto Head of Engineering up until this point, and by handing off the entire Engineering function to a new hire, can bring up the question of "what am I going to do?"

In my post on Hypothesis Sheets, I argued that:

As a founder, you should always be de-risking the business's top risks

and that's applicable here. Someone external can likely do the undifferentiated-to-your-company work of running the operations of the Engineering team (people management, hiring, ensuring projects run on-track), leaving the founder/CTO free to work on problems that are unique to the business and therefore better suited to a founder tackling.

When hiring a new VPE, the CTO will likely shift their role. In From Founder to CTO, Calvin French-Owen (co-founder of Segment) lays out 4 archetypes it's common for founder/CTOs to step into:

1. People Leader (VPE): growing the Engineering org and making sure it runs effectively
2. Architect: thinking about the technology primitives and next-gen system architecture for the company that will unlock new capabilities or efficiency
3. R&D: pushing the company toward new, unproven big product opportunities (often through months of uncertainty)
4. Marketing/Customer-facing: focusing on marketing and interacting with customers (and especially helpful if you market to developers)

CTOs who are Head of EPD (see above) are effectively choosing (1) but for all of the EPD functions: likely running the day-to-day planning, project execution, people management, and hiring for all three functions. But by hiring a VPE, Non-Product CTOs are effectively giving up that first path. These CTOs should decide on becoming, (2), (3), (4), or something else that is critical to the business!

Deciding on this will also help you figure out who the VPE will report to: the CTO or the CEO². I was surprised at how many search firms tried to insist that candidates would need to report to the CEO in order to be able to recruit great candidates, but I have not found that to be true. You should choose the reporting structure that makes the most sense for yourself and your business and not let candidates or recruiters dictate that for you³.

Creating a rubric & interview guide

Once you think you need a VPE, it's likely already, frankly, too late and with hiring timelines (3-9 months), they'll feel "late" by the time they join 😂⁴. That being said, before⁵ you start sourcing and interviewing people, take the time to narrow down and figure out exactly what you're looking for.

Here's the process I used to create a rubric and interview guide. I think hiring an "executive" can seem intimidating for many founders (myself included), but I quickly realized that hiring managers is very similar to hiring ICs: people management is a skill—like coding—that you can create a rubric for and then interviews to test against those skills.

So the algorithm (created by Erik Goldman) for creating the rubric and interview plan for a VPE is the same one I use for IC roles:

1. Write down what the person will be doing for the next 6-12 months (with a heavy emphasis on the 6 part).
2. Write down a list of questions you'd need to say yes to in order to feel comfortable bringing them on (e.g. "can they manage projects without a full-time PM?", etc.)
3. Group the questions into related groups and give those groups descriptive titles—these are your hiring traits. If you have more than three of them, you're probably not going to find someone and you might need to pare back your expectations for the hire.
4. Write interviews that, when summed together, give overlapping signal on the hiring traits (assume that a good candidate will randomly flub one interview for no reason—you should be resilient to that) and answer the questions to produce a yes/no hiring decision.

Your interview panel, combined with thoughtful referencing⁶, should likely be a mix of hands-on work, interviews, and potentially a take-home/writing sample. I used to be skeptical of behavioral interviews, but a well-run behavioral interview can pull out a lot of signal.

You should probably do this exercise yourself and come up with a rubric that's specific to your company and what you're hiring for, but if you'd like to see the rubric & interview plan I came up with, contact me.

Do you really need a VPE or just an Engineering Manager?

The next question to ask yourself is what level of person are you looking to hire⁷?

If the person will:

• be an IC to start
• have no clear path to team growth

then it's likely OK to hire a line Engineering Manager or "Director" level person to start!

On the other hand, if the person will:

• immediately or has a clear path to managing managers
• have a sizeable team already in-place

then it's likely you do actually need a VPE! When hiring a VPE, you should be ready & willing to defer ownership over the entire Engineering function to the person you hire.

Meet great people to calibrate

If you've never hired a VPE before, one great trick to help you calibrate is to try to meet 3-5 excellent people from your network who have done the job before and have great reputations. Try to get connected and do an intro call with these folks, maybe under the guise of getting feedback on your rubric or advice for hiring. Worst case: you can calibrate on what "great" looks like for this role. Best case: you can be surprised and recruit someone who you initially thought was out of your reach.

Hiring

OK, you've decided you're going to hire a VPE, met 3-5 amazing candidates, and created a rubric and interview plan. Now it's time to start actually finding folks to hire. Hiring an exec is similar to hiring for other roles: source applicants⁸, run an amazing hiring pipeline, assess the candidate, and sell/close⁹, but with one exception: you have the option to hire an executive search firm.

Deciding to hire an Executive Search firm or not?

How should you decide whether to hire an exec search firm? I suggest spending ~2 weeks leveraging your network to see how many candidates you can source organically before hiring a firm. If you have an incredible network/brand and can source this way, you'll save a lot of money! In our case, we spent 2 weeks self sourcing and realized pretty quickly that if we wanted to hire this person on any reasonable timeframe¹⁰, we would have to utilize a search firm.

Choosing a Search Firm

I recommend talking to at least 2-3 partners before deciding (as with all vendors/contractors). You should choose someone—the specific person, not the firm—that you jive with and you think can understand and pitch your business well. I found that smaller firms can often do a better job than some of the name-brand larger firms for a company of our size. The search partner should also have a great network of VPE-level folks and be able to get candidates on the phone¹¹.

A few other notes on selecting a search partner:

1. Be sure the person who is "selling the search" is the same person who will be executing the search (the person who is reaching out/interviewing potential candidates and in the details). For larger firms, there may be a risk that the senior person you talk to during the sales process then has a more-junior person executing the search day-to-day.
2. Make sure to ask for a list of the partner's previous searches/experience: not the firm overall, but the specific individual who led each search.
3. One question you can use to interview the search partner is to ask them to pitch your business back to you and see how they do and how comfortable they are with the material.
4. Another interview question: ask the search firm for a few candidate ideas, e.g. who would you reach out to first for this search? And do you think they will respond? This can test a few things:
   1. are you aligned on profile
   2. do you have the same "taste" in prospective target companies/candidates
   3. do they know the prospect and if they have any interest in a startup? is this a prior relationship or a cold outreach?

To find search partners, ask for recommendations from your investors and other founders who have done similar searches to help get introduced. I worked with a great Engineering search partner, Alex Zakupowsky of Fusion Talent, who I'm happy to connect you with if you'd like: contact me for an intro.

A note on titles

When you hire the person, you might be tempted to give them a "VPE" title (as I've been using throughout this essay). But I actually recommend trying to use the "Head of Engineering" title instead. "Head of" is a really versatile title: it allows you to signal the person's importance in the org (both internally and externally), without setting precedence on level. If the person performs spectacularly, you can promote them to "VP" as the org grows, or if not, you have the flexibility to layer them with a VP in the future¹². At a fast growing startup, I think it's expected that execs will either rise to the occasion as the company grows or be replaced within 18-36 months depending on the company and their personal growth. Stripe, for example, was famous for only using the "Head of" title even as they grew to thousands of people.

A note on internal alignment

Assuming you already have an existing Engineering team in-place, you will want to bring them along so they are bought-in (to the extent possible) on the hiring decision (of their new manager / skip level). While you want to bring your team along, you should remember—and remind them—that you will be taking their feedback (e.g. interview feedback, if they are on the panel) into account, but that you will be making the final hire/no-hire decision¹³.

This can be particularly tricky if you're replacing a current person in the role vs. hiring someone net-new. If you're doing a replacement, you have a couple options: if you have someone who can step in on an interim basis, you can let go of the current person and then start cleanly with a search and the whole team is involved throughout. But if you can't muster being VPE-less for that long, you may need to start sourcing in secret and then only tell the team once you have line-of-sight to a hire (e.g. 2-3 onsites scheduled).

Conclusion: good luck!

Hiring an exec is hard, it can feel scary, but being intentional and structured about the process you use can make it less so! The skills needed to be a VPE, including people management skills, are accessible just like the IC skills (e.g. coding) that you're used to interviewing for. Apply the same interview practices you use for other roles, optionally with a search partner and with an internal comms plan, and you'll be good to go. Good luck!

Thanks to Hannah Squier, Laura Hilton, Ryan Seekely, Alex Zakupowsky, and Gavin Nachbar for reading and providing feedback on early drafts of this post!

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